1,2-Dichloroethane → HCID 22990071, compound

HRID 1169426Notes

Reaction equation

HRID 1169426 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH2:11][CH2:12][O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)=[CH:17][C:15]=3[CH:16]=2)=[O:9])[CH2:4][CH2:3]1.[O:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:49]CCCl>>[ClH:49].[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:19]=[CH:20][C:14]3[O:13][CH2:12][CH2:11][C:10]([C:8]([N:5]4[CH2:6][CH2:7][CH:2]([NH:1][CH:31]5[CH2:32][CH2:33][O:28][CH2:29][CH2:30]5)[CH2:3][CH2:4]4)=[O:9])=[CH:16][C:15]=3[CH:17]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 22990165HCID 22990165, compound

Product 1

HCID 22990071HCID 22990071, compound

Procedure

To 4-amino-1-(7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbonyl)piperidine (0.3 g) and tetrahydro-4H-pyran-4-one (0.083 g) dissolved in 1,2-dichloroethane (6 ml) was added under ice cooling sodium triacetoxyborohydride (0.25 g), and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was evaporated to remove the solvent, was neutralized with a 1 N aqueous solution of sodium hydroxide and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and then was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent, and the residue dissolved in ethyl acetate was mixed with 4 N hydrochloric acid/ethyl acetate (0.5 ml) to collect the precipitated powder by filtration. The powder was washed with hexane to obtain 1-(7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbonyl)-4-((tetrahydropyran-4-yl)amino)piperidine hydrochloride (compound 77) (0.35 g) as a colorless amorphous substance.

Workup

  1. additionwas added under ice
  2. customThe reaction mixture was evaporated
  3. customto remove the solvent
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialan aqueous saturated solution of sodium chloride, and then was dried with anhydrous magnesium sulfate
  7. customThe resulting organic layer was evaporated under reduced pressure
  8. customto remove the solvent
  9. dissolutionthe residue dissolved in ethyl acetate
  10. additionwas mixed with 4 N hydrochloric acid/ethyl acetate (0.5 ml)
  11. customto collect the precipitated powder
  12. filtrationby filtration
  13. washThe powder was washed with hexane

Sources & evidence

ORD record
ord-80b671d5b77643d3b992abf122883ac5
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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